Teachings

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Professor
ENZO CADONI (Tit.)
Period
First Semester 
Teaching style
Convenzionale 
Lingua Insegnamento
ITALIANO 



Informazioni aggiuntive

Course Curriculum CFU Length(h)
[60/69]  CHEMICAL SCIENCES [69/00 - Ord. 2019]  PERCORSO COMUNE 6 56

Objectives

The course design and synthesis with lab aims to provide the student:
1. a methodological approach to the design and carrying out of an organic synthesis
2. The basic principles and issues of the retrosynthetic analysis
3. The main reactions that are currently used in organic synthesis with particular emphasis on the mechanistic and stereochemical aspects.
Within the synthetic plan, the student must be able to recognize the principal reagents, to recognize and to explain the different types of reactions and their mechanism, propose possible synthetic routes for obtaining simple compounds.
In the laboratory, students will refine manual skills acquired in previous courses, work independently, be able to solve the real problems of organic synthesis and relate the experimental aspects of the concepts learned in the theoretical part.

Prerequisites

basic organic chemistry: main organic reactions and their mechanisms, functional groups and their reactivity, the fundamental concepts of stereochemistry

Contents

Pericyclic reactions
( electrocyclic, sigmatropic, cycloaddition )
The principle of conservation of orbital symmetry
Coupling reactions
Heck, Suzuki and Negishi
Various reactions:
Mannich, Wittig, Sharpless oxydation, Cope oxy-Cope, Diels-Alder, Robison anellated, pinacolic rearrangement, Claisen rearrangement Conia-ene reaction metallazione reactions
Retrosynthetic approach
fundamental principles
Molecular complexity, Retron, types of transformations +
Retrosyinthetic strategies:types.
Strategies based on transformations
retrosynthetic analysis and synthesis of fumagillol, Squalene, antibiotic X206
strategies based on the starting materials
retrosynthetic analysis and synthesis of 'helminthosporal and picrotoxinin
topological strategies
disconnection of acyclic systems, disconnection of cyclic systems with isolated rings, rings fused disconnect, disconnected systems to bridge the disconnect spirocompounds
stereochemical strategies
stereochemistry complexity, chiral centers "clearable"
strategies based on the transformation of functional groups
Use of functional groups equivalent
protection of functional groups
reactions unpolung
simultaneous use of different strategies
retrosynthetic analysis and synthesis of longifolene, the poratine and perhydrohist rionicotoxin
Lab
Carrying out of two or three synthesis developed in the theoretical.

Teaching Methods

The lessons will be lectures with projection of slides; the content of each slide will be presented in detail and discussed. The teacher will ask questions to push students to participate actively to the lesson, to formulate hypotheses and to propose possible solutions to the problems considered . With regard to the lab, students will make the experience in group, but in any case the work will be conducted, from the beginning to the end of the synthesis, in an independent way as much as possible. The teacher will help the students only when, after repeated attempts, they won’t manage to find the solution. The teacher will ask the students to consider the meaning of the operations performed and to reconnect them to the concepts examined in the theoretical part.

Lectures: 32 hours- laboratory activities: 24 hours. Laboratory performed with groups of two, maximum 3 students. Practical execution carried out by each student

Verification of learning

Report of the laboratory activity.
The final exam will be an oral dissertation where the student will be required to enucleate his lab experiences, explain basis concepts faced during the course. The student will be required not to keep in mind the concepts but to be able to explain fundamental concepts and the involved reactions. The student, in fact, will show the retrosynthetic processes by exploiting the slides used by the teacher during his course.

Texts

Morrison Boyd, chimica organica, casa editrice ambrosiana
Tsuji- Trost palladium catalysts and reagent,
Corey the logical of chemical synthesis, Wiley Interscience

More Information

Slides available to students

Questionnaire and social

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